When O’Shaughnessy told us that “we are the music makers, we are the dreamers of dreams,” he gave us more than a nine-stanza poem about musicians and how their undying love of their art builds the world around them. Though he may wax poetic over the art form, he also gives us some insights into those who tell stories through music.

A Chicago-area music maker with big dreams, Steve Grand rose to fame practically overnight when his country-themed music video for his song “All-American Boy”—which features the story of a gay youth who has fallen for his straight friend—went viral in 2013. (Grand graced the cover of OutSmart in August of that year.)

Grand will once again land in Houston to sing and inspire a local audience at The Diana Foundation’s Country Dinner Weekend that takes place October 2–4. Grand is the guest performer on October 2 and 3.

Since 2013, Grand has been busy. With a career forming around him and the LGBT community ready to welcome him in as one of their own, Grand sold his downtown Chicago apartment and traveled abroad, advocating for the community at many Pride parades—even teaching master classes for the next generation of musicians in Lithuania.

Although he has yet to begin planning his next album, Grand assures his loving followers that he’s always writing, always recording, and always making music, having grown and cultivated his team over the last two years to include not only himself, but also a booking agent and managers—a step up from his “All-American Boy” days when he funded the acclaimed music video with $7,000 of his own money.

While building momentum for himself, Grand’s current ideas and aspirations as an artist are just as big as they were in 2013. Grand generously spoke with OutSmart about his hopes for a future album of mixed-genre music, and what his “dream collaboration” would look like.

“I’m really into Hozier right now. I think he’s just a different kind of songwriter. It would be good for me to collaborate with him—I think I’d learn a lot from him,” he says in regard to Irish singer and songwriter Andrew Hozier-Byrne.

Big plans don’t happen immediately—they take time, planning, marketing, and money. Grand’s initial success came quickly, but it came at a price. His “All-American Boy” video piled up a big bill that Grand is still paying back on his own, while also booking shows and travelling.

Despite the hectic fun of the past two years, Grand has managed to keep his head above water, and has done so with humor and humility. The good-humored all-American Midwesterner, who started out playing piano for a local church, is just as goofy as the rest of us. “I just cut off all my hair. I didn’t realize how funny-shaped my head was, but it was like some symbolic way of purging myself. I just wanted something fresh, just clean . . . you know, just press the reset button,” Grand laughs. “And I pretend I can grow a beard, but it’s just really patchy. I’m thinking of just coloring in the rest of it, because I just really want a beard.”

Beard or no beard, Grand’s charming personality and musical style continue to endear him to us, one Internet video release (or Diana concert) at a time.

What: Steve Grand at the Diana Foundation’s Country Dinner WeekendWhen: October 2 and 3Where: VariousDetails:thedianafoundation.org